


A League of Their Own

by brightsee



Category: Arrow (TV 2012)
Genre: Alternate Universe - Baseball, Baseball Player Oliver, F/M, Fluff, Single Mom Felicity
Language: English
Status: In-Progress
Published: 2015-08-10
Updated: 2015-08-27
Packaged: 2018-04-13 21:55:55
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 9,245
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4538868
Author URL: https://archiveofourown.org/users/brightsee/pseuds/brightsee
Summary: <blockquote class="userstuff">
              <p>Felicity never imagined this to be her life: her son crashing into Oliver Queen in the grocery store, Oliver Queen coming to her son's baseball game, and going on a date with Oliver Queen.</p>
            </blockquote>





	1. first encounter

**Author's Note:**

> hey all! this oneshot came about from a seeing a recent video of a little girl crashing Ronda Rousey's open training session, the idea of pro ball player Oliver Queen, needing more single mom!felicity, and needing some fluff in my life. I'm currently working on this huge angsty three shot and just needed some sunshine and rainbows, this came out and I kinda love the idea. Hope y'all enjoy.

Felicity Smoak loves grocery shopping for the week, to have a list and collect everything needed. It makes her feel organized and gives her a sense of accomplishment when she returns home with bags of groceries needing put away. It’s been her favourite thing to do since she was little and helped her mother, but now that she is a mother she finds it slightly more difficult. 

Sebastian has a mind of his own, much like she did at that age, and sometimes he just doesn’t listen to her when she tells him to stay close. He sees something that interests him and the minute that Felicity is looking away and grabbing an item he disappears. He’s never far, always within sight but never within arms reach which sometimes is frustrating to Felicity. 

This trip to the grocery store is no different. 

Her son is eight years old and has an obsession with baseball and the Starling City Rockets, always seen sporting the black cap with the signature red Rockets logo. He’s currently standing beside her in the produce talking about an upcoming little league game, he’s talkative just like Felicity, when he drops his sentence and grows quiet. 

Felicity has her attention on picking the right apples, making sure there are no bruises, when she notices the sudden silence. She immediately feels the absence beside her and quickly glances up, ready to run after Sebastian. Her son is ten feet ahead of her, running towards something, and when he collides with a set of legs he quickly wraps his arms around them. 

Felicity drops the apple in her hand, abandons her cart, and takes off after Sebastian who is already chatting away to the stranger. He’s smiling from ear to ear and Felicity is so focused on Sebastian that she doesn’t register what he’s saying or who he’s talking to. 

“Sebastian Joshua Smoak!” Felicity yells, marching across the open space towards her son. 

Sebastian turns his head, blue eyes growing wide and steps back from the stranger. “Mom!” he exclaims, his mood dimming slightly. “I didn’t mean to run away but-”

“No, Sebastian, you can’t just run away on me like that. What if someone had grabbed you and tried to take you from me?” She questions, bending down so they were eye to eye. “I don’t mean to scare you but I just don’t want anything to happen to you.”

“I know, I’m sorry, but I saw Oliver Queen!”

Felicity knows immediately who Oliver Queen is because not only does she work for his family’s company, Queen Consolidated, but also because he’s a pitcher for the Rockets. The man is Sebastian’s favourite baseball player and the only reason he’s working so hard to become a pitcher for his little league team. 

Sebastian turns around, his smile already back. “Oliver, this is my mom.”

Felicity straightens and extends her hand, “Felicity Smoak.”

“Oliver Queen,” he greets, reaching out and shaking her hand. Felicity notes that his is much larger than hers, rougher with calluses lining the pads of his fingers. “It’s nice to meet you.”

Felicity pulls her hand back and blushes under his intense gaze. She’s seen a few pictures of him, mostly in the morning paper which she always skipped over, but he’s much more prettier in person. He’s got that rugged look about him with the stubble lining his cheeks and his plaid shirt rolled up to his elbows. 

“I’m so sorry about Sebastian,” she begins but is immediately cut off by her son. 

“Mom, it’s okay. We’re totally friends now.”

She looks down at her son who’s smiling up at her, brown hair falling into his eyes, and he just looks so happy. “You’re friends are you?” She asks, gaze flicking from Sebastian to Oliver. 

“Totally,” the boy beams before turning back to Oliver. “I saw your last game and that home run was amazing! I wish we got to go see more of your games but watching from home is alright too. But I don’t catch every game because Mom said I have to finish my homework before I watch T.V. and science is hard, you know?”

Oliver chuckles lowly under his breath, “I remember science being quite difficult.”

“Yeah but math is way too easy, how does that even make sense? My Mom says I’m a genius like her but I don’t think I want to build computers when I grow up. I think that’s what she does?” His ramble makes Felicity proud because that’s another thing he gets from her, except he’s never embarrassed when he goes off on a tangent. 

Sebastian loses track of his thought, shakes his head and continues. “The point is she’s smart and works with computers but I don’t want to do that. I want to be a professional baseball player, just like you!”

Felicity squeezes his shoulders, drawing his attention. “Yes, but school comes first remember?”

Sebastian rolls his eyes and Oliver smiles up at her. “I agree with your Mom, school is really important and should always come first.”

“We’ll see,” he replies with a shrug of his shoulders. “You should come to one of my baseball games!”

“Sebastian, honey-” she tries to interrupt but her son bulldozes on in a whirlwind of words. 

“I play at Regent Park every Tuesdays and Thursdays but game days are Thursdays. I’m pitching this week and that’s the position I really want to play. Short stop is cool, and first base is pretty fun, but pitching is the best position,” he says, finally finishing and looking up at Oliver expectantly. 

Felicity doesn’t want to see the hurt on her son’s face because he just asked Oliver Queen something that’s impossible for someone of his status. Sebastian is still young and doesn’t understand that Oliver has better things to do than go to a little league game and is most likely busy training or on the road. 

She bends down on one knee and turns Sebastian towards her, his smile slowly fading when he catches sight of her worried look. “Buddy, Mr. Queen is really busy with his own baseball games and practices that he won’t have time for yours.”

“Oh,” he replies, looking down at his shoes. 

“Do you remember when his next game is?” Felicity asks, hoping to help him understand better. 

“On Friday against the Twins.”

She gives him a small smile of encouragement. “That’s right, and Minnesota is really far from Starling City.”

“How far?” Sebastian asks, raising an eyebrow. 

“2, 000 miles, or a whole day to get there if he drove,” Felicity explains carefully. 

Sebastian nods and turns around to address Oliver. “You’ll be very far away, too far away to come to my games.”

“I’m sorry,” he apologizes and Felicity notes that it looks like he actually means it. 

“It’s okay,” he shrugs, bouncing back, his smile growing. “I’ll just watch you on TV and watch you hit more home runs.”

Oliver chuckles and nods, “I’ll try.”

“I can’t wait to tell everyone I met Oliver Queen. This is the best moment of my entire life!” He roars, beaming up at Oliver. “Good Luck against the Twins.”

“Thanks, Sebastian,” Oliver reaches out and fist bumps the boy’s awaiting fist. 

Felicity steps forward, “I’m so sorry for interrupting your Sunday. Thank you for everything, Mr. Queen.” 

Oliver waves it off, “Call me Oliver, Mr. Queen is my father and I am no where close to the business man he is.”

“I’ve noticed,” she blurts, and when she catches her blunder closes her eyes tight and opens them as she tries to backtrack. “Not in a creepy way or anything, it’s just I’ve worked with your father over at Queen Consolidated. He’s very professional-not saying that you aren’t or anything, it’s just he’s always in a suit and tie and you’re...”

She waves at his body as she trails off because he’s the exact opposite of his father, but in a good way. Felicity is momentarily distracted by his attire because it looks entirely too good on him. Her gaze travelling over his muscular arms, his hands shoved into his front pockets, only accentuating his muscles. When she meets his eyes again he’s smirking, entirely too smug for her liking. 

“I’m a baseball player, not really one for suits unless I have to,” he winks, finishing her train of thought. 

Felicity blushes and the shifting of her son in front of her catches her attention and she remembers exactly where she is. “Well thank you for everything, Oliver, but we’ll let you get back to your grocery shopping. Good luck with the season.”

Oliver smiles and gives them a small nod before continuing on with his shopping. Felicity can’t help but replay those moments because she just met a major league baseball player and embarrassed herself remarkably. Sebastian can’t stop talking about that moment because he met his idol and it was everything the boy hoped it would be. 

-

Weeks go by and Sebastian still talks about that moment, mostly to his friends or when he see’s Oliver playing on television. Felicity doesn’t think much of it or the game that he was invited to until Oliver Queen actually shows up to Regent Park one Thursday night. 

Felicity is so wrapped up in the game that she doesn’t notice someone sit down beside her on the worn down bleachers. It’s only when Sebastian is up to bat moments later and she’s screaming for him to run when he hits the ball that when the play stops and she sits back down she almost sits on someone. 

She silences a scream but places distance between her and the body she almost sat on, embarrassed of the possibility it was another parent. When Felicity turns to look at the person beside her it’s Oliver Queen biting down a laugh, his blue eyes alight with amusement. 

“Oh my gosh, Oliver, you scared me!” She hisses and scoots closer to him as to not draw attention from the other parents. She’s feeling slightly selfish but she knows he’s here for her son and doesn’t want others to steal his attention. “What are you doing here?”

“I was invited,” he laughs, the corner of his eyes crinkling. “I hope you don’t mind dropping in like this.”

“No it’s fine, I’m sure Sebastian will love this!” She insists happily. “He’s been talking about meeting you for weeks and to be honest I’m kind of thankful. Now whenever he doesn’t want to do his homework on game nights all I have to say is your name and he gets back to it. It’s a lifesaver, seriously, you have no idea.”

“I think I can imagine,” Oliver replies. “Sorry I couldn’t come sooner.”

Felicity reaches out and gives his arm a squeeze. “You didn’t even have to come, meeting you has been the highlight of his year. Really, you didn’t have to do any more for him.”

“I wanted to,” he replies honestly. “He’s a great kid and I couldn’t stop thinking about that day at the grocery store.”

“Same here, I was mortified after that meeting,” she groans. “Seriously, I’m not sure who has it worst with the whole babbling gene, me or Sebastian.”

“It’s cute,” Oliver says, a hint of a smile on his lips. “On both of you.”

Felicity searches his eyes for the hint of anything and finds sincerity in them. Before she could say anything the crowd around them roars to life, parents standing on the surrounding bleachers and clapping. Felicity looks up in time to see Sebastian sliding across home plate. 

This time when she stands up cheering Oliver is right beside her and clapping. She can’t help but watch him out of the corner of her eye, at the flex of his arms and his encouraging cheers for her son. Sebastian gets up and brushes of the dirt, lighting up when he looks up to the stands and sees Oliver Queen cheering him on. 

When they sit back down Felicity leans towards him and whispers, “I think you just made his life and when the game ends you’ll have very excited twenty eight year olds all wanting an autograph.”

“It’s a good thing I came prepared,” he jokes, pointing down to a bag that she hadn’t noticed before. “I grabbed enough Rockets caps for the two teams and my baseball card which my agent threw in there before I left.”

“Oliver,” she sighs, “you really didn’t have to do that.”

“Felicity, I wanted to,” he argues giving her hand a squeeze to end her protests. “Now lets get back to the game, these eight year olds really know how to play.”

Felicity feels a smile cross her lips and when she turns to watch the next batter up from her sons team, she sees out of the corner of her eye that Oliver is smiling too. He gives her shoulder a nudge with his and she immediately relaxes, forgetting that she’s sitting beside Oliver Queen.

They talk a little throughout the rest of the game. She learns he’s grown up in Starling City, opting for a baseball career instead of becoming a CEO, and how his parents eventually got on board. She tells him about growing up in Vegas, anecdotes about Sebastian, and moving to Starling only three years ago. 

The Dodgers, Sebastian’s team, wins 10-8 and the team celebrates with popsicles provided by the designated weekly teammate. Sebastian runs up the stands and jumps into Oliver’s arms. He’s quick to catch the boy, arms closing in around his smaller body. 

Sebastian pulls back and looks up at Oliver excitedly. “Did you see that slide in the third inning?”

“I did,” he laughs, “it was awesome, buddy.”

“And we won! You have to come meet my team.” Sebastian demands, already sliding away from Oliver and tugging on his hand to follow. 

Felicity gives him an apologetic smile when he looks back at her with a lost expression. She just follows behind, grabbing the bag of goodies he brought for the kids. Once onto the field Oliver is immediately swept up into a whirlwind of eight year olds all clammering for his attention. 

When he’s finally able to come for air they’re ushered off the field for another game that was ready to be started up. Felicity joins him, handing him the bag of goodies and watches with amusement as the twenty or so kids grow excited. Sebastian stands beside Oliver looking a little smug, his smile never wavering, as he stares up at his idol. 

They take a group picture with the two teams, red and blue jerseys all surrounding Oliver. Felicity watches as parents clammer together to get pictures of their child and a Major League Baseball player. When that’s done, he hands out a cap to each child and his player card which holds his stats on the back. 

Everyone is smiling and each child scrambles for a minute of Oliver’s time which he happily obliges, bending down to shake their hand and get an individual picture. Sebastian is with a few teammates, gesturing wildly with his hands and capturing their attention with a story of some kind. Felicity stands back from the crowd, a few mothers coming up to talk to her about her connection to Oliver Queen, others keeping their distance and sending disapproving and jealous looks her way. 

After a half hour of Oliver taking pictures with players and excited fans the crowd disperses leaving him alone. She watches him take a deep breath, the smile never leaving his lips, and walks over to Sebastian. They say a few words before making their way to Felicity. 

“Can we go for ice cream?” Sebastian asks the second he’s in front of Felicity. She takes a moment to consider because it’s growing late and he still has school tomorrow. “Oliver asked if we can go.”

Oliver looks a little guilty. "It was more of a suggestion, if you were okay with it.”

Felicity chews on her lip looking down at her hopeful son and back to Oliver whose expression mirrored Sebastian. She couldn’t resist the two sets of blue eyes, Sebastian's slightly darker than Olivers, but both pleading with her to say yes. 

“Oh, alright, we’ll go for ice cream,” she replies with fake exasperation. “It’s not everyday that we get invited to ice cream by Oliver Queen,” Felicity adds, sending a Oliver a wink.

Sebastian jumps up in excitement. "Come on, Oliver.”

Felicity picks up Sebastian's abandoned equipment bag and follows after the two. Sebastian has forgone his blue team cap and switched to the new Rockets cap that Oliver handed out earlier. The two are discussing the game up ahead, Oliver stepping in when Sebastian takes a breath to give his input. 

The ice cream shop is just across the street and whoever came up with the location is both brilliant and a menace. Felicity has repeatedly had to talk Sebastian out of ice cream after his games because too much sugar before bed is not something she enjoys. She’ll let this one slide because it’s Oliver Queen and she couldn’t find it within herself to say no to either of them. 

Of course when they enter the little shop Oliver draws the attention of almost every patron, neither he or Sebastian notice. Felicity limits Sebastian's order to one scoop of chocolate, Oliver follows suit, and Felicity orders a scoop of vanilla. They take a seat outside on the patio at a small table where Sebastian resumes talking about his game. 

“And did you see in the fifth I struck that one kid out?” He questions Oliver, looking up at him proud. 

“Yeah, I did, it was great!” He replies with enthusiasm. “Your form was pretty good too, with more practice you’ll be amazing.”

“Will you help me?” 

Felicity feels her stomach drop at the question her son just asked because she doesn’t want to get his hopes up. Felicity knows that Oliver was just being generous before by showing up at Sebastian’s game, goodies included, but it was just a one time thing. She really doesn’t expect anything more out of him, but her son is still young and doesn’t understand these things. 

She’s about to reply for Oliver when he steps in and answers. “I would love to help out, if it’s alright with your mom.”

Felicity stares at Oliver in shock, her grip tightening on her cone. “You’d do that?”

He just shrugs and his smile grows, “I want to. I do manage to spend quite a lot of time here in Starling, away games don’t take me away for too long.”

“Well if you’re up to teaching an eight year old,” she says, wanting to warm him it’s no easy feat. 

“Oh, he’s up to it,” Sebastian interrupts, answering for Oliver. 

He just chuckles. "It sounds like I’m up to it.”

“Are you sure though? It’s just it’s a lot to ask for and a lot for you to give, I don’t want to take you away from any obligations. You have a family and a probably a girlfriend and things you need to do besides help out a kid you just met and-”

Oliver cuts her off mid ramble with his hand reaching out and squeezing hers. “How about an hour on a Monday nights? You won’t be taking me away from any obligations, there’s no girlfriend and I do family get togethers usually on the weekend. If you don’t want me to help out then I would completely understand.”

“No, we want your help!” Sebastian exclaims, drawing the attention back to him. “Please, Mom?”

Felicity is caught again between the two of them both with pleading expressions. “Well, who am I to stand in the way? Monday’s are perfect.”

“Sweet! Oliver, you can teach me to throw a curveball. I’ll be the best pitcher in the league.”

Oliver reaches out and ruffles Sebastian’s hair. "How about we’ll take it one step at a time.”

“Okay,” the boy sighs and takes a lick of his melting ice cream. 

Felicity gives him a small smile when she notices him looking at her with an unreadable expression. She’s come to learn that Oliver Queen is a mystery and a half and if there’s one thing that Felicity is not a fan of it’s mysteries. She’s not really opposed to these Monday nights if it means making her son happy and getting more time to get to know Oliver. 

After that they stick to more neutral topics. Sebastian tells Oliver about school, then about his team and friends. Oliver tells Sebastian all about being a professional player, what it’s like to travel, and stories from the road. Felicity just listens to their easy conversation, sometimes adding in her own input or asking questions. 

Felicity loves that Sebastian absolutely adores Oliver and that he’s actually getting to know his idol, knowing some kids never get the chance. She’s thankful that Oliver is so patient and giving with Sebastian, adding to the fact that he’s gorgeous and she may have the slightest crush on him. 

When the sun begins to lower in the sky Felicity feels a little guilty for splitting up the party but she sees Sebastian growing tired as it nears his bed time. They finished their ice cream half an hour ago but the conversation was easy and continued despite their treat being done. They have been thankfully left undisturbed, people watching Oliver from afar but to scared or nervous to confront him. 

When Sebastian lets out a yawn Felicity knows that it’s time to pack it up. “I think it’s getting close to someone’s bedtime,” she announces when there’s a lull in conversation. 

Oliver chuckles. "How did you know?”

That causes a fit of giggles from Sebastian and that’s when Felicity knows he’s close to passing out. “I was talking about the little one. Sebastian, can you go clean up, you have chocolate all over your face.”

Sebastian nods and slides out of his chair, heading back inside the ice cream shop to clean up. That leaves just the two of them. “I didn’t know the great Oliver Queen’s bedtime was 8:30,” Felicity teases.

“There’s a lot you don’t know about me,” he winks. “Maybe another date and we can learn more about each other?”

“Another date?” Felicity questions, wondering when they’ve had their first date.

“Wouldn’t you consider this a date? We watched a baseball game and went out for ice cream after, seems like a date to me,” Oliver replies, unable to contain his smirk. 

“I guess so but usually dates don’t include my eight year old son.”

“The more the merrier,” Oliver declares. “But if you’d like our next date to be the two of us, that can easily be arranged.”

Felicity chews on her bottom lip, he’s just so damn smooth. “Are you always this charming?”

Oliver’s smile grows and it looks really good on him. “Go on a date with me and you’ll find out.”

She really can’t deny him or the way he’s looking at her. “Alright, alright, I’ll go on a date with you,” she laughs, giving in. 

They exchange numbers and work out the logistics for Monday night, both unable to contain their smile. Sebastian returns with clean hands and mouth and they say their goodbyes, Sebastian clinging to Oliver for a moment longer than expected. 

“I can’t wait for Monday,” he mumbles when he pulls back from the hug. “Thank you, Oliver.”

“Anytime, buddy,” he replies softly, giving him one last fist bump. Oliver turns to Felicity, “I’ll see you Monday, and maybe we can talk more about that date.”

“I look forward to it,” she says, stepping toward Oliver. She gently places her hand on his shoulder and reaches up and plants a soft kiss to his cheek. “Thank you for everything, you’ve really made a lot of people happy today,” she whispers into his ear. Felicity pulls back and gives him a smile, “we’ll see you Monday, Oliver.”

“See you Monday.”

Felicity feels his eyes on them as they cross the street and head back towards their car. She never would have thought this would be her life but she’s really happy that they went grocery shopping that Sunday and that Sebastian in his unattained excitement had introduced himself to Oliver. There’s something about him and it’s a little early but Felicity can tell that he’ll be in their life for a long time.


	2. date night

**Notes for the Chapter:**

> hey all, I'm back! I wasn't sure if I would be able to continue this and was having a few issues writing it (I hate writing dates) but I pushed through. I think this will turn out as a series of one shots, pure fluff with no real big plot or anything. I was overwhelmed by the response the first chapter got, and thank you everyone who commented, kudo'd, and reviewed. 
> 
> A huge thank you to Alyssa for editing and listening to me complain about this fic for the past three weeks, she's my rock. Also thank you for all the suggestions, they have been noted and will most likely be incorporated. Thanks to thesmoakingswan, you gave me me the idea for the ending and I hope I executed it well enough. Anyway, enough of all that, I hope you enjoy this next part.

Felicity is a ball of nerves. 

Oliver is set to pick her up in twenty minutes and she’s not even close to being ready. Sebastian is perched on her bed flipping through a comic book and is no help. Everytime she holds up a dress for his opinion he pinches his lips and thinks about it for a moment too long before shrugging it off. 

“Honey, you need to help me pick out a dress for tonight,” she says as she comes out of the closet with two dresses in her hands. None of her clothes are up to date with current fashion standards She has a son so she’s been a little preoccupied to go shopping. Besides what little money that she has left over after each pay check is split between her savings and Sebastian’s college fund. 

Sebastian pokes his head up from his comic book. “They all look the same.”

Felicity sighs because they don’t all look the same. The handful of dresses she’s picked out have been sun dresses of varying colours and designs, not one looking like the other. Her top two picks are between a solid red with lace and a soft yellow floral print. She studies the two dresses in her hand, holding one up at a time in front of her as she studies her appearance in the mirror. 

“Do you think this one looks like a 1950’s house wife?” Felicity asks, turning around and holding up the yellow sundress. 

Sebastian looks at her confused, brows furrowed. “I don’t even know what that is.”

“I need to get myself a girlfriend,” she mumbles under her breath, turning back around to study the dresses in the mirror again. 

She eyes Sebastian through the mirror who has his nose back in the Captain America comic book, almost completely lost to the world. Felicity’s about to comment about homework because she knows that he has a book report due soon and he still has chapters left to read when a voice rings through the small townhouse. 

“King Roy of the babysitters is here for Lord Bass Master!” The voice shouts, followed by the closing of the front door. 

Felicity smiles to herself and turns just in time to catch Sebastian scrambling from her bed and running out the door and down the stairs. There’s a ruckus downstairs and when Roy enters her bedroom Sebastian is thrown over his shoulder giggling. “Hey, blondie,” he nods, depositing her son on the bed and flopping down next to him.

“Which one?” She questions, holding up the two dresses. 

Roy contemplates it for a minute before pointing to the red dress. “The other one looks too much like a librarian, the red one is hot.”

Felicity scrunches up her nose because Roy is like her little brother and she did not need to hear that. She studies the red one and it’s settled, she’s wearing it because it’s cute and not as outdated as all the others. “Okay, Mama’s got to change, out both of you.”

The two boys roll off the bed and hurry out the door leaving Felicity ten minutes to get ready. She closes her bedroom door and quickly changes into the dress, pinning her hair up so the curls fall effortlessly down her back, and applies make up. One of the things she’s learned to accomplish since becoming a mother is the ability to get ready in under ten minutes. 

She’s putting the finishing touches on her makeup and slips a pair of hanging jeweled earrings and checking her appearance. Felicity turns slowly in the mirror and falls in love with the dress, the lace adding texture, the cut out in the back showing off skin, and the red colour vibrant against her skin. 

With a deep breath she grabs her clutch which holds only the essentials and makes her way down the stairs. Felicity pauses halfway when she hears voices that aren’t just Roy or Sebastian, but a deep voice that sounds a lot like Oliver. Her plan was to never leave Oliver alone with Roy, who is ferociously protective of her and Sebastian which stems from years of friendship. 

Felicity braces herself for what she’s about to witness when she enters the family room at the bottom of the stairs to her right. Oliver is seated on one couch with Sebastian and Roy seated on the couch opposite, both studying Oliver with serious eyes. 

She steps into the room and interrupts, “Oliver, hi.”

Oliver stands up immediately, letting out a breath of both relief and amazement when he sees her. “Wow, you look beautiful.”

“Thanks,” She blushes, his gaze focused solely on her. He’s dressed in grey dress pants and a light blue button up shirt, his attire having a casual feel to it. Felicity realizes she’s been staring at Oliver a little too long and that they’re not the only ones in the room, introductions are in order. “Oliver, this is Roy.”

“We’ve met,” Roy informs her, speaking up from the couch. He’s still staring at Oliver, brows drawn and eyes narrowed, doing his best to intimidate the older man. 

“Right,” she murmurs, chewing on her lip for a second when her nerves take over. Felicity quickly pushes them away, and turns back to Oliver. “Ready to go?”

“Yeah,” he replies, and Felicity hesitates for a moment because did Oliver Queen sound nervous? 

Felicity turns to the remaining two boys on the couch. "Please don’t destroy the house, and try to limit yourselves to one snack each, give Sebastian a bath, and make sure he gets to bed at a reasonable time.”

“Yes, Ma’am,” Roy salutes, smirking at her. She knows he’s only going to follow half of her rules but he’s good with Sebastian so she really can’t complain.

Sebastian slides off the couch and gives her a quick hug goodbye. Felicity notices that he’s trying to hide a smile and peers up at Oliver under his eyelashes, trying desperately to appear unaffected by being in the presence of his idol. 

Oliver and Sebastian have had two Monday night practices so far and every time Sebastian is excited to learn from Oliver Queen that it’s all he can talk about for the remainder of the week. The only reason why he’s so quiet now is because of Roy, who must have said something to the boy. She’s not worried about the change of behaviour and if resumes further will address it. 

“Okay,” she huffs, standing back up to her full height. With a squeeze of Sebastian’s shoulder and a pointed look towards Roy she’s ready to leave. “Have a good night you two.”

“Have fun, Blondie,” Roy smirks. 

“Bye, Mom,” Sebastian says from his seat beside Roy on the couch. 

She turns towards Oliver giving him a smile. "Ready?”

Oliver nods, holding his arm out for her to lead the way. She escorts him to the front door and ushers him out into the warm summer air. Felicity asked for their date to be early enough so that she could make it home at an early time in case Sebastian needed anything. Oliver happily obliged, setting their date for six o’clock. 

At the end of the walkway sat a Bentley, she’s not a fan of cars but it looks ten times more expensive than her old Honda Civic. She tries to appear unfazed as Oliver opens the passenger door and she slides onto smooth Italian leather seats. Of course Oliver Queen would have a ridiculously expensive car, he’s a pro baseball player and an heir to a fortune 500 company. 

When Oliver slides in beside her, Felicity feels her nerves grow tenfold. She’s going on a date with Oliver Queen. Alone. The past few times they’ve spent time together Sebastian has always been there as a buffer between the two, now she’s worried they’ll have nothing in common or worse he won’t even like her once he learns more about her. 

Felicity is drawn from her thoughts when she feels a firm squeeze around her hands, drawing a halt to her fidgeting hands and draws her gaze up to look at Oliver. “I can practically hear you thinking,” he says softly, giving her a small but concerned smile

She releases her lower lips which she hadn’t realized was caught between her teeth. “Just nervous, you’re Oliver Queen.”

Oliver kinks one eyebrow looking thoroughly amused. “I am Oliver Queen.”

“You’re Oliver Queen, a major league baseball player and the son of my boss’ boss. I’m just some woman you met in a grocery store one afternoon who has a son that idolizes you. It’s just crazy and a little hard to wrap my brain around,” she elaborates, her voice wavering.

“How do you think I feel? I’m going on a date with this incredible woman who is way out of my league. She’s too smart for her own good, what if I say something stupid and embarrass myself?” He shares, his hand giving hers a final squeeze of reassurance. 

Felicity relaxes at his words, finally giving him a smile. His only grows and she catches sight of his dimples, feeling more relaxed then she did moments ago. “So where are we going?” 

“It’s a surprise,” Oliver replies, turning in his seat and buckles up. 

Felicity follows his lead and does up her own seat belt and feels the smooth hum as the car comes to life. “Would it completely ruin the mood if I told you I wasn’t a fan of surprises?”

“Not at all, but do you trust me?”

Without hesitation and with all honesty, she replies. "Of course.”

Oliver reaches over the console and gives her hand a squeeze. “So what else aren’t you a fan of?”

“Mysteries,” she blurts, her filter clearly failing as she continues on. “I hate them and they just eat at me until I solve them. It’s how I got into computers, something was wrong with a crappy school computer and I took it apart and fixed it without the teacher knowing. I got a week worth of detentions but it was love at first sight and now I’m head of the I.T. department at QC.” 

Felicity takes a deep breath and adds one more thing. "And clowns, I hate them.”

Oliver chuckles. "Good to know. Is there a reason behind it?”

“That’s a story for another time. But how about you, what’s one of your fears?” She questions, turning in her seat slightly to see his lips twitch in amusement. 

“Open water, had a bad experience with my dad a few years ago. I think I may be the only wealthy person who will not step foot on their own family yacht,” he responds lightly but there’s something in his expression that tells her there’s more to the story but she doesn’t push it. 

They’re already into downtown Starling through the business district, passing by Queen Consolidated, when Felicity notices they’re heading into Little Italy. It’s a six block lane that houses an assortment of Italian restaurants, bakeries, and shops. “I hope you like Italian,” Oliver suggests, looking slightly nervous as he pulls to a stop in front of a valet service. 

“I love it actually.” Felicity stares up at the sign reading ‘Donatello’ and is pleased that it’s the one restaurant in Little Italy that she hasn’t had a chance to try yet. 

The restaurant is on the fancier side of the fellow family oriented restaurants, with a valet service and all, which is why she hasn’t been yet. She’s pretty sure if she brought Sebastian that many people would look down at her and she doesn’t have many friends in the city outside the office. So this surprise by Oliver is very welcomed. 

Felicity is pulled from her thoughts as Oliver opens her door and helps her out of the car. She’s swept inside, hand clasped firmly in the crook of Oliver’s elbow, and revels at the interior of the classic Italian restaurant. 

She doesn’t notice the stares of other patrons, or the way the young hostess glares at Felicity as she leads them to their table, but she does catch the wink Oliver gives her when he helps her into his seat. When he’s finally sitting across from her, Felicity finally takes a deep breath and takes it all in. The man across from her, under the dim light wearing the pale blue dress shirt that brings out his eyes and tan skin makes her stomach flutter and flip and suddenly the nerves are back.

When the waitress stops by their table making introductions, Oliver asks for a bottle of red wine. It’s an expensive wine and she’s a little confused how he knew what she liked to drink. He smiles sheepishly at her, “I saw the bottle of red last Monday in your fridge. I wasn’t snooping. I’m sorry. I shouldn’t have assumed...I should have asked.”

“Usually I’m the one talking in sentence fragments,” she smirks. Oliver looks away and Felicity thinks she sees a hint of a blush on his cheeks. “I love red wine, thank you.”

At that moment the waitress returns and fills up two glasses of red one, placing one in front of Felicity then Oliver, and leaves the bottle. Felicity takes a sip and it’s probably the best red wine she’s ever tasted. The menu has an exclusive menu and everything just looks so good that she can’t decide what to order. 

“What is the best item on the menu?” She asks, holding her menu down so she can see Oliver over the rim. 

He purses his lips and thinks about it. “Cannelloni ai carciofi.”

“I don’t think I’ve ever had it, but I’ll take your word for it,” she says and closes her menu, placing it on the table. It’s a pasta dish with artichokes in it, which sounded interesting and delicious to Felicity. 

Oliver follows suit and when the waiter returns he places both their orders and even initiates a brief conversation with the waitress in Italian. She’s pleasantly surprised because the sound of his voice and the dialect makes him even more attractive. 

“I didn’t know you spoke Italian,” Felicity inquires, raising an eyebrow. 

“I know the basic conversation sentences. I’m more fluent in Russian and Mandarin,” he replies, and when she nods for him to keep going, Oliver explains. “We spent quite a few summers in China for QC and my housekeeper was Russian and she taught my sister and I.”

“Wow, that’s kind of amazing,” she gasps, astonished by his multilingualism. 

Oliver shrugs. “Not as amazing as your accomplishments. You finished MIT at 19, right? Then got your Masters on top of that, with a baby. Seriously, that’s impressive, Felicity.”

“How did you know all that?” she questions, brows quirked with curiosity. 

“I can't reveal my sources, Ms. Smoak,” he smirks, taking a sip of his wine. 

Felicity leans forward in her seat. "Have you been asking around about me, Mr. Queen?” 

“No, well, maybe?” He says, his voice growing softer as if he’s embarrassed. “I mentioned in passing about my date tonight and my father overheard and couldn’t stop praising you. I think you’re one of his favourite department heads.”

She perks up at that, smiling wide. “Well the I.T. department was a mess when I came in, had to revamp the firewall, train some of the employees, and update the servers. The guy before me was really not qualified to run a department, and let’s just say he didn’t last long with the new changes we made.”

“Wow, no wonder he likes you.”

“I’m good at my job, and it’s way better than managing a tech store, I was way overqualified there,” she states nonchalantly before taking a sip of her wine. The rich taste shocks her senses and reminds Felicity that she’s drinking fancy wine and on a date with Oliver Queen and talking about work. “But we really shouldn’t talk about work.”

“But I like talking about work if it involves you.”

Felicity blushes. "You really are this charming all the time aren’t you.”

Oliver winks. "Yup.”

“Well how about you take a break from being charming and tell me about how you got into your profession,” she prompts. 

“I thought we weren’t going to talk about work,” he smirks, his cheeks dimpling. 

“Fine, what do you want to talk about?”

“You,” Oliver answers quickly, leaning forward and locking eyes. A retort is on the tip of her tongue and he must sense it because he finishes his thought. “And Roy.”

“You want to talk about my relationship with Roy?” She asks, double checking that was his intended purpose. 

“Yeah, the kid seems really protective of you and Sebastian, there has to be a story there. I’d like to hear it if you’re willing.”

He’s really too charming for his own good, she notes. Oliver is staring at her with such interest, that she can really tell that he cares about her and learning about the important people in her life. Besides, she’s beginning to realize that she really wants to share these things with him. 

“He was my next door neighbor in Vegas,” she begins, smiling at the memory of a little blonde haired boy running around with a red cape. “We both had single mothers who worked crazy long hours, his wasn’t there as much as mine was. Roy’s about six years younger, so most of the time I ended up taking him to school and watching him afterwards.”

Felicity takes a second to gather her thoughts knowing the next part was hard to talk about. “One day when Roy was ten, his mother didn’t come home. He became a child of the state after that and I was off to M.I.T. but we still kept in touch. When I returned home at twenty-one with a baby in tow, he was fifteen and getting into a lot of trouble. My mom didn’t really want to but we ended up fostering him as long as he straightened out, which he did. A few years later he followed me here to Starling City, he helped with Sebastian and still does even though he moved out a year ago.”

Oliver reaches across the table and gives her hand a squeeze. “He’s your little brother, you needed to protect him.”

“He didn’t say anything to you before I came downstairs before, did he? Because you seemed a little off and Sebastian was staring at you funny and Roy was being Roy, and something was obviously said.”

“Just the typical guy thing, If I break your heart he’s going to break me,” he confesses, a lilt of amusement to his voice. “Which I took very seriously.”

Felicity laughs. "Don’t pay any attention to Roy.”

“He reminds me a lot of my younger sister,” Oliver states. “Thea always used to interrupt my dates. She’s ten years younger, so when I was a teenager and started bringing girls home to watch movies, she would always sneak downstairs and sit right in between me and my date. Later on, when she got older, she would just call me and interrupt with some emergency.”

“She loves you, it’s so cute,” Felicity chuckles.

“My dates didn’t think so,” Oliver grumbles. “I learned eventually to lock the door or turn off my cell phone. Thankfully she’s grown out of that habit.”

She’s about to reply but the server swoops in and places their meals down on the table in front of them. Felicity gasps at the meal, how delicate but delicious it looks. Oliver gives her a slight nod and smile prompting her to dig in. The pasta dish is different from what she’s ever tried, the artichokes adding the perfect addition to the sauces. 

After her first bite, she washes it down with a sip of her wine which complements her meal perfectly. “This is so good.”

“It’s my favourite dish, I’m glad you like it,”

The rest of the meal is spent appreciating the dish and trading stories about siblings and parents. Felicity told Oliver of the time when Roy was eight and put gum into Felicity’s hair which resulted in an impromptu haircut for both of them when she retaliated. Oliver relayed with a story of Thea when she was six and decided to give herself a haircut just like his, their mother was not very happy with that development. 

There was laughter as they shared stories of them growing up. The subjects were light, even when they moved to Felicity talking about Sebastian and how he was almost identical to Roy growing up. They shared the same love for exploring and adventure, which Felicity was sure going to give her grey hair in her late twenties. 

When their plates were taken away, Oliver reached across and links his fingers with hers. He runs his thumb over her knuckles, stopping momentarily to play with the ring on her forefinger, then continues to run his thumb over the back of her hand, and repeats. It was soothing, and as they continued talking about insequential things, she relished in the feeling of his hand linked with hers.

Felicity finishes the last little bit of the wine and Oliver suggests they forgo dessert because he has other ideas in mind. Their waitress, who Felicity just realizes is a young woman, smiles at them and places the cheque down on the table and disappears. Oliver opens it, scans it quickly before placing his card on top. Felicity notices a heart drawn across the bill and blushes, realizing the waitress has witnessed their public display of affection. 

“So where are we going for dessert?” Felicity asks the moment they step out of the restaurant and into the warm summer air. 

The street lights are on, casting a warm glow across Oliver’s face. “There’s a little ice cream cart across the street in the park that’s one of my favourites.”

“Sounds good, lead the way,” she says, smiling up at him. 

Oliver reaches for her hand, linking fingers again, and leads her across the empty street and towards the park. She squeezes his hand just to make sure that it’s all real, and it is because he looks down at her and gives her a wide, generous smile. 

The parks is well lit, the walkway lined with string lights setting the mood. There’s other people milling about, couples walking dogs and teenagers hanging out on a park bench. The ice cream cart is located not far from the entrance of the park and it’s an older man serving and he seems to be on a first name basis with Oliver. They make a bit of small talk while he gets their cones ready, Felicity ordering Vanilla and Oliver with Chocolate. 

Oliver says his goodbyes and leads Felicity to walk down the path, farther into the park. “Ice cream seems to be our thing.”

“I guess it is,” she agrees taking a lick of her ice cream. 

When they find an empty park bench, Oliver suggests to sit down making it a little easier to finish their dessert. Felicity thinks back to the last time they had ice cream just last week. “I don’t want to sound like a broken record but you really didn’t have to volunteer your time to help with Sebastian, or even go to his game.”

Oliver turns so he’s facing towards her. “I wanted to.”

“But why? You’re so busy with your work schedule and we’re just strangers that you have no obligation to.”

“I know,” he nods. “But there was something about Sebastian, and you, something telling me that I had to get to know you both. And it’s really not a problem with my schedule, Sebastian told me he understands if I can’t make it to every Monday night practice.”

That answer takes her breath away. “You’re kind of an amazing guy, you know that, Oliver Queen?”

“Would I still be amazing if I said that part of me really wanted to get to know you as well?” 

“Yes, and I’m really grateful for everything you’re doing,” she says. “It means the world to Sebastian and I.”

“And I’m grateful that you’re letting me into both of your lives,” he counters smoothly with a small smile. There’s a moment of silence where Felicity is thinking of how to reply and hide her blush, when Oliver grows serious again. “I don’t mean to intrude but I was just wondering about Sebastian’s father.”

“He’s not...he’s...it’s complicated,” Felicity stumbles out, tense and unsure how to explain it all to Oliver. 

Oliver places his hand on her back and rubs circles. “You don’t have to talk about it now, I just didn’t want to be intruding or stepping on anyone’s toes.”

Felicity’s heart beat returns to normal as she grows calmer. “Thank you, and we will talk about it, just not tonight. There’s no need to ruin a perfect night.”

Oliver nods and pulls Felicity into his side and loops his arm across her shoulder. They finish their ice cream in silence, Felicity snuggles up beside him breathing in his cologne. She finishes her cone before him and closes her eyes, just embracing his warmth and solid body. 

Once Oliver finishes they sit and talk for a few moments longer, the light air of their date returning, and not long after he’s walking her back to his car. His arm remains over her shoulder the whole walk back, his hand sweeping down her back when he helps her into the car. As he drives, his hand finds hers and he drives one handed. 

Felicity is enjoying the little touches, and as he drives her thumb is running along the back of his hand. They make small talk and Oliver suggests another one of his favourite restaurants for their next date which surprises Felicity. “A second date?” She inquires, raising a brow. 

Oliver pulls to a stop outside her house and turns to look at her. "Would you like to go on a second date with me, Felicity?”

“I would love to,” she smirks, reaching across and giving his cheek a kiss. The action stuns Oliver and he sits there staring at her, car still humming, as she pushes the passengers door open and gets out. She walks up the path, hearing the commotion of Oliver getting out of his car and following behind. 

“I’m sure Sebastian is still up, if you’d like to say goodnight to him,” she suggests when they reach the door. Oliver smiles and follows her into the house, and just as she’s predicted, Sebastian is sitting at the bottom of the stairs by the front door. 

“We’re home, Roy,” Felicity yells out into the house. 

Roy walks out of kitchen, shrugging on his coat. “Perfect timing, I just got called into work.” He ruffles Sebastian’s hair as he passes, gives Felicity a quick one-armed hug, and leaves. He stops as he’s halfway out the door, “also Sebastian didn’t learn anything from me.”

Felicity turns to question just what exactly that means but Roy’s already out the door, slamming it behind him and effectively cutting off any questioning. So she turns her attention to her son who is staring at Oliver intently. 

“What’s going on?” She questions, but is ignored. 

“I need to talk to Oliver,” Sebastian says, gaze never wavering. 

Felicity turns to Oliver who just shrugs, just as confused as she is. He steps forward and sits down on the stairs beside Sebastian, “What’s up, buddy?”

Sebastian looks over at her and raises his eyebrows telling Felicity she’s not in on the conversation. “Right, I’ll just be in the kitchen.”

Felicity moves just around the corner so she’s not seen but can hear the conversation, a little curious and concerned. The silence doesn’t stretch too thin before Sebastian is talking. “Roy says that I’m the man of the house,” he begins, his tone very serious for an eight year old. “Do you like my mom?”

“I do,” Oliver replies quickly. “And I like you as well.”

“But you’re not going to make her sad are you?” 

“No, never, why would you think that?”

There’s a brief pause before Sebastian speaks again. “The last guy left, just like my dad, and that made her sad. I like you, Oliver, but I don’t want you to make her sad.” 

“I’m not going to make either of you sad,” Oliver promises. 

“Good, or else I’ll have to beat you up,” Sebastian says seriously. 

“Let’s hope it doesn’t come to that.”

There’s commotion and then Sebastian’s laughter rings through the house and Oliver yells. "You can come out now, Felicity.”

She slips from her hiding place and see’s Sebastian wrapped up in Oliver’s arms, trying to get away as Oliver tickles him. “Bed time, young man. Say goodnight to Oliver.”

Sebastian pouts but just reaches up and gives Oliver a hug. "Good night.”

“Night buddy,” Oliver whispers as he lets go of the boy and watches as he trudges up the stairs slowly. When Sebastian enters his room, Oliver stands up from his spot on the stairs. “Did you hear all that?” Felicity nods. “I meant it, everything I said. I don’t plan on going anywhere.”

“It’s been one date, how can you make these promises?” She questions, worried not only for herself but for her son who idolizes Oliver. 

“I have a feeling and if you trust me, I promise not to let you down,” he says, his eyes relaying every bit of the truth he’s trying to convey. 

Felicity gives in. “I trust you.”

Oliver smiles and brings her in for a hug. He leans his head down so his mouth is beside her ear, “I won’t lead you wrong.”

Felicity’s heart flutters, the feeling unfamiliar but welcomed. She’s a little reluctant to pull back, but does a few moments later when Oliver releases her from his grasp. His hands settle on her shoulders giving them a light squeeze. “I have a series of away games but my next home game should be in a few weeks, would you two like to come?”

“Yes! Please, Mom?!” Sebastian yells from the top of the stairs. 

Both Oliver and Felicity laugh. “I guess that’s a yes,” she answers. 

“Perfect, then maybe after the three of us can do something?”

“Sounds good.”

“I’ll see you Monday for my practice with Sebastian.” He leans down and gives her a kiss on the cheek. “Good night, Felicity,”

“Good night, Oliver.”

She sees him out and then turns to look up at her son who is still standing at the top of the stairs, “This is the best night ever!”

Felicity shakes her head and laughs, unable to believe that this is really her life. “Yeah, it’s the best night. Now let’s get you to bed.”

**Notes for the Chapter:**

> thoughts? what would you like to see next?


End file.
